


Close Enough

by thewinchesterlifestyle



Category: Supernatural
Genre: Bottom Dean, Dirty Talk, F/M, Fingering, Pegging, Pre-Supernatural (TV), Rough Sex, Size Kink, Strap-Ons, Sub Dean, Twink Dean, but the d/s tones are very light, kind of
Language: English
Status: Completed
Published: 2016-07-26
Updated: 2016-07-26
Packaged: 2018-07-27 00:05:16
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,410
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7595569
Author URL: https://archiveofourown.org/users/thewinchesterlifestyle/pseuds/thewinchesterlifestyle
Summary: <blockquote class="userstuff">
              <p>Dean wants nothing more than to find himself moaning under a man but that is far from what his dad expects from him. But a woman at in a bar offers him something that might be as close as he's going to get.</p>
            </blockquote>





	Close Enough

**Author's Note:**

> Written for a prompt.

Dean forced himself to look away from the attractive older man at the end of the bar. He tried to ignore the quick flashes of fantasy that involved him going home with the man and spending the night getting fucked. That wasn’t what was expected of him and he mentally scowled at himself before turning to the drink in front of him.

His father would be disappointed in him. Probably too disgusted to form words.

“You look lost in thought.” The voice had him turning to see a beautiful woman with a teasing grin and dark hair that fell down around her shoulders in soft looking curls. “Something bothering you?”

He let his eyes move over her body and then Dean found himself putting on one of his more charming grins. “Not anymore.” It earned him a smile and she was leaning closer to him.

“Good.” Her lips curved, “You look better with a smile on that handsome face of yours.” The comment had Dean blinking before he relaxed on his stool. “Now how about you buy us a round of drinks and if you’re interested I wouldn’t mind getting to know you better.” It was obvious she didn’t see the point in dancing around the subject and Dean found it refreshing.

“Know what you want already?” he signaled the bartender to order their drinks and turned his full attention to the attractive woman next to him. “What’s your name?”

“Holly.”

“Dean.”

Two hours later they were slamming Holly's bedroom door shut and the two of them were quick to remove every single article of clothing from the other person’s body. “Fuck.” Dean breathed when her fingers dug into his arm and she nipped at his neck with a wicked grin.

“Would you like me to fuck you?” the question had him jerking and looking at her with slightly dazed green eyes. “I was thinking about pegging you but if you’re not interested we could do something else.” Her smile was easy and gave away nothing. It didn’t let him know that she had noticed him looking at men in the bar and the obvious restraint he’d used to deny himself.

“Pegging?” Dean tested the word and watched as she stepped away from him to move across the room. When she finally came back Holly held a rather impressive strap on and a bottle of lube. He glanced up at her face, the light expression there, before offering a slightly cheeky grin in response. “I’m up for trying something new.”

The response had her eyes brightening as she indicated for the bed, “Whatever position you think will be easiest to take my cock.” The words had a noticeable effect on Dean who almost moaned at the thought as he glanced at the impressively large attachment once more.

It was long and thick, a good size, where it hung from its straps in her almost dainty hands. “Do you have one you would recommend?”

“I wouldn’t mind seeing that pretty ass of yours raised up in the air for me so I can finger fuck you.” The way Dean started and his mouth dropped open had a laugh escaping. Holly slowly shrugged and offered an amused grin, “I know what I want.” There wasn’t a hint of shame and it was more than refreshing.

He climbed onto the bed, could feel her moving up after him, until a warm hand pressed against the place between his shoulder blades to help guide him into a more submissive looking position. Holly moved around him, adjusting him so his legs were under him but spread and braced wide while his ass was raised up, until she was satisfied.

“There we go.” Her warm hand stroked down his back and over the swell of his ass before the sound of a cap popping open caught Dean’s attention, “Have you ever had anything in your ass before?” she stroked two slick fingers over Dean’s tight hole and silently waited for a response.

“A finger or two.” He mumbled but she only nodded and continued her same motions until he relaxed.

 _There we go_  she thought and started to press in the first finger. Holly went slow as she started to prep Dean until she began to actively search for Dean’s prostate. When she found the bundle of nerves Dean shivered and moaned, clenching tight around her, even as he shoved back into her fingers. He lazily began to fuck himself back on her fingers instinctively seeking to pull them deeper.

“Fuck.” Dean breathed out and shifted himself as Holly kept working her fingers inside him until she was satisfied. He could hear movement behind him and it wasn’t until he felt the blunt pressure at his hole that he realized she was about to fuck him. “ _Oh_.” His mouth dropped open as Holly slowly split him open on the head of her fake cock. He could feel it stretching him, burning fiercely, and filling him up until she had bottomed out inside him.

Green eyes slid closed and Dean panted as Holly drew back before snapping forward. Her hands gripped onto him, tightly, as she started to snap her hips forward at a quick and punishing rhythm that didn’t give him any time to adjust to having something so large buried inside him for the first time. It ached and his erection had flagged at the unexpected pain but the longer she pounded into him, occasionally managing to send pleasure lighting up inside him, the more he got into it.

Soon it was everything Dean had imaged being fucked open would feel like.

He let himself get lost in the feeling of a cock moving inside his ass and the occasional brush of it against his prostate even as his mind replaced the beautiful woman with the man from the bar. Dean let himself imagine he had gone home that unknown man, that it wasn’t a toy inside him but instead a real cock, as moans slipped from his lips and his cock slowly hardened once more.

“That’s it.” He barely registered the praising voice behind him and instead reached to stroke his cock only for a hand to stop him. “That’s mine too.” That same voice spoke and a hand, slick with lube, wrapped around him and started to stroke him quickly. It teased the head of his cock before moving away and he reached to grip himself now.

Dean knew the exact grip and speed he wanted, jacking himself off in time with Holly's thrusts, until his body stilled and he came with a moan. “Fuck. Oh.” He breathed and stared almost blearily at the pillows in front of him as Holly kept thrusting inside him.

He could feel her grinding against his ass, the toy inside him now vibrating, as she started to moan. “Yes.” The sensation of the toy vibrating against his prostate was almost too much but he could feel her grinding against him and the sensation of the vibrations was driving him insane.

Dean hadn’t gotten a good look at the toy but he was thinking of investing in one for future partners if the sex felt that good. It would be the closest he could get to the feeling of a guy fucking him and he wasn’t going to let it go.

Her motions eventually stilled and he heard the pleasured moan as she enjoyed her orgasm. “Haven’t done this in a while.” Her voice finally sounded and it was almost disappointment that it wasn’t really a man still inside him.

Slowly the length in him withdrew and he was empty, ass clenching on air, as Holly took off her toy and left it on the sheets as she sprawled out next to him. When he looked he could see a pleased and sated expression on her features, a flush to her cheeks, as she gazed at him with hooded eyes. The disappointment was now almost crushing but Dean shoved it aside and moved away from the mess he’d made on her sheets.

“I think that toy might be my favorite.” She reached out to touch him, “I wasn’t sure about fucking you with it vibrating but the night is young and we can try that next.” Dean was about to speak until she continued, “Or I could ride you.” Now she was grinning again and Dean found himself responding to the feisty woman next to him. “Your choice.”


End file.
